Reading the story 'My Sexual Awakening' of Sept 11 reminded me of my own sexual awakening, which was very similar to his, also through wearing a T-shirt for jammies the first time. In my case it was my mother who introduced my brother (3 years older than me) and me to the T-shirt wearing.
I was 8 at the time and we went to visit my aunt, uncle and cousin (my mother's sister had just given birth to my cousin) for a week during summer holidays. The first evening at bedtime (brother and I were to sleep on a mattress in the living room) mother told us to get changed into our jammies. We couldn't find any jammies in our suitcases and reported it back to mother who admitted she forgot to pack any for us. She then said we could sleep in the T-shirts we were wearing but to remove our pants. While removing our shoes and pants, brother asked mother if we should keep our underwear on at which she said no, it was unhealthy to wear underwear while sleeping.
Our T-shirts weren't very big and didn't even cover our butts so both of us jumped into bed very quickly after taking our underwear off. Instinct made my hand go straight to my willy once in bed and I started squeezing it getting a hardon quickly. Lying next to my brother I could see from the movement under the covers he was doing the same. A couple of minutes after we got into bed, mother said goodnight and switched the light off. Brother whispered it felt nice not wearing pants and I agreed, watching his hand moving more vigorously under the covers in the semi dark.
'What are you doing?' I asked and he answered he was jacking off. I had no idea what he meant and asked him. ' Making my willy feel good idiot,' he answered. I wasn't sure how to do it but started rubbing my willy and it felt reel good. While rubbing it, I watched brother and got a fright when he suddenly lifted his hips high and shivered before falling back. 'What happened?' I asked scared. He answered nothing and turned on his side facing away from me. I carried on rubbing my willy as it started feeling really good. After a few minutes I understood what happened to brother when I got the most wonderful feeling in my crotch.
That whole week followed the same pattern; we would remove our clothes except our T-shirts, get into bed and start playing with ourselves until reaching orgasms. My brother always reached an orgasm before me. He probably also had dry ones because I don't recall him wiping afterward.
While at my aunt's, we showered in the morning where at home we used to bath at night an hour or so before bedtime after which we would put our jammies on and our first night back at home it was my turn to bath first. After drying myself I walked to my room, took out some jammies and got dressed into them as I always used to do. When mother sent us to bed and I got into bed, I suddenly remembered my pleasurable sessions at my aunt's and put my hand inside my pants getting an immediate hardon. I started rubbing my willie as usually but the restriction of my jammies made it more difficult and I pulled them down a little. It still didn't feel right so I pulled my pants off completely, finished the job and forgot about putting my pants back on.
The next morning I woke with my bed covers on the floor (something that happened often when it was a hot night) and my mother busy opening the curtains. I suddenly realized I was without pants but it was too late to hide it from my mother and thought she was going to give me a scolding but she just picked up my covers from the floor and pulled them over me. She gave me a kiss and said good morning. We went shopping after breakfast and to my surprise, mother stopped at the boys clothing section and started looking at nightshirts. She asked if we would like to have some nightshirts rather than jammies and both of us agreed eagerly but to our disappointment she looked at the prices and said it was too expensive. We followed her to the men's section where she stopped at the T-shirts and told us to select a couple each.
That first evening I couldn't wait to go and bath so I could wear my new nightshirt (T-shirt) and had my bath even before dinner. Going to bed was also something to look forward to so I could play with myself and it happened regularly almost every night. When I was 11 I started masturbating more than once a day often and had my first cum before I was 12.